Guesthouse vacation rentals in Florida Keys

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Florida Keys

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

A private pool glistens under the sun, surrounded by lush palm trees. Two pink loungers rest on the water's edge, enhancing the relaxing atmosphere. The serene view includes a glimpse of the New River, adding to the tranquil setting.

Guesthouse in Fort Lauderdale

4.92 out of 5 average rating, 108 reviews

Guest Suite - Private Pool! 15 Minutes to Beaches

Picture yourself relaxing at a PRIVATE pool not shared with other guests! Casita Del Rio, a stunning vacation rental on the New River in Ft. Lauderdale, FL! This private guest suite offers exclusive comfort with an upscale bathroom, refrigerator, microwave, and Keurig. The pool area is, exclusively yours, with loungers for basking in the sun. Book your unforgettable escape less than 20 minutes away from Ft. Lauderdale's stunning beaches, restaurants, and so much more. Questions? Message us :)

Superhost

A bedroom setting features a spacious bed with light yellow bedding and a wooden headboard. A rustic sliding barn door is visible, accompanied by a mirror. A rocking chair adds character, while soft natural light filters through the room.

Guesthouse in Homestead

4.86 out of 5 average rating, 105 reviews

The Farm Keys experience New and adorable Unit 2

Kick back and relax in this stylish space. Modern country decoration, separate bedroom, bathroom, fully equipped kitchen, common area with sofa bed, washer and dryer, patio, barbecue and seats for your enjoy. Everything you need to feel at home!This convenient location is near to the Bay Side Parks, Everglades Park (The largest subtropical wilderness in the United States) many great beaches and entertaining night life in the Florida Keys!! Perfect choice for those traveling to Miami or the Keys!

Guest favorite

Guesthouse in Key Largo

4.87 out of 5 average rating, 446 reviews

Romantic Cabin/Guesthouse, beach Sunsets, fishing.

Private Romantic Bayside Cabin/Guesthouse, peaceful settings, lovely sunsets, beach, fishing pier, lush gardens surrounded by nature and wildlife, birds, iguanas, manatees, dolphin’s, eagles, the beach is just a short walk away from the Guesthouse enjoying a cocktail, fishing, boats cruising by, kayaking, snorkeling or an amazing sunset. *This Guesthouse is on bayside not Bayfront ! Same property but private from the residence! "No pets, Airbnb-granted pets Exemption cus allergies reasons"

Top guest favorite

A tropical tiki hut features natural thatched roofing and wooden flooring, offering a relaxed seating area with a central coffee table. Surrounding greenery enhances the peaceful ambiance, while a scooter is visible in the background, suggesting a convenient way to explore the area.

Guesthouse in Biscayne Park

4.95 out of 5 average rating, 499 reviews

Cozy and charming cottage

Our cottage is located in a very quiet residential area, 15mn to the beach (Bal Harbor area).20mn from both Miami and Fort Lauderdale Airports, Located in the backyard of the main house but separate and with an independent entry. Enjoy our tropical garden and beautiful pool, in the back of our house. Share with owner only, we give priority to our guests to enjoy it! Parking available in our front yard. No kitchen but microwave and fridge. TV, cable and WIFI. It is suggested to have a car.

Top guest favorite

Guesthouse in Miami

4.98 out of 5 average rating, 187 reviews

Casanessa - a private cottage among the gardens

103 years old with a fresh new look! Come we just revamped our gardens! Relax in this spacious, recently renovated one bedroom cottage detached from the main house with its own living room & kitchen. Surround yourself with peaceful greenery & gardens while being steps away from the heart of Calle Ocho's art galleries & restaurants. Local bakery, grocery store, & laundromat are around the corner at your convenience. We offer coffee, tea , 2 water bottles, snacks & free street parking.

Guest favorite

A vibrant dock area is shown with lined jet skis ready for rental. A thatched-roof building offers shaded seating with colorful umbrellas. Lush palm trees sway gently in the backdrop, enhancing the waterfront experience under a clear blue sky.

Guesthouse in Key Largo

4.93 out of 5 average rating, 136 reviews

Seaside Bungalow

Very private entire Cottage brand new walking distance to world famous Tiki Bar jet ski rentals kayaks Extremely private surrounded by exotic flowers and orchids.Less than 2 miles from Baker's Cay and close to the Key Largo and Islamorada wedding venues. We have a fully stocked home size kitchen. All the condiments coffee creamers sugar ketchup mustard etc. Giant stone shower with shampoos and conditioner and plenty of plush towels. Beach towels and chairs as well as 2 bicycles.

Guest favorite

A spacious bedroom features a comfortable bed with neatly arranged towels on top. Large sliding glass doors open to a private outdoor area, where a pool is visible, surrounded by greenery. Stylish wooden beams adorn the ceiling, enhancing the room's spacious feel.

Guesthouse in Miami

4.91 out of 5 average rating, 187 reviews

Chic Guest house with pool, hot tub and bbq area

Enjoy a stylish experience at this centrally-located place. Close to everything miami has to offer Some answers to common questions below —— About 7 minutes from the cruise ship terminals (virgin, carnival, Royal Caribbean, Norwegian cruise lines etc About 10-15 minutes from Miami International Airport Yes the pool and backyard is private and you won’t be sharing with any other guests. You are the only guests when staying on my property.

Superhost

The exterior view of the bungalow showcases a light-colored façade with white trim. Two wooden steamer chairs sit invitingly on a concrete porch, alongside a decorative potted plant. A turquoise door adds a pop of color, complemented by large windows adorned with shutters.

Guesthouse in Key Largo

4.89 out of 5 average rating, 252 reviews

Oceanside, 1 bedroom, Bungalow in Key Largo

Canal front bungalow with beautiful views of the ocean. Private water front and pergola with steamer chairs and hammock. BBQ your fresh catch while lounging on the back porch, relaxing in the tropical landscape. One bedroom with Queen bed. Queen size pull-out couch in the living-room. Full kitchen boasting high-end appliances. One Car Parking by unit. Centrally located between shopping centers and destination activities.

Guest favorite

A stone pathway lined with smooth pebbles leads through a lush garden area, featuring greenery on either side. Two horses can be seen walking in the open field beyond, with a white farmhouse and fencing in the background under a clear sky.

Guesthouse in Homestead

4.96 out of 5 average rating, 136 reviews

Villa Samsara - on a beautiful 5 acre farm

When you come and stay with us, it’s a deeply immersive experience with our horses. Often you will find them in your front door or window. There is something profoundly impactful about being around horses and sharing close-quarters with them. You are in their energy field, receiving all that they have to offer. Without even realizing it, your energies are being grounded and regulated through their presence.

Guest favorite

A bright entryway showcases a green door with a modern keyless entry system. A round mirror is mounted on the wall, reflecting light into the space. A stylish table with two stools is positioned near the window, adorned with decorative items and tableware.

Guesthouse in Miami

4.99 out of 5 average rating, 324 reviews

Chic Studio - Near Everything Trendy

Welcome to our chic hideaway! Inspired by the unique Miami art deco style, our space invites you to wind down and relax after a long day exploring the magic city ✧ If shopping, art, and dining are your thing...you’re in for a treat! Driving you are only: • 5 minutes to Wynwood, Miami Design District & Midtown • 15 minutes to South Beach • 15 minutes to MIA airport • 15 minutes to Downtown/Brickell

Guest favorite

A clear blue pool is framed by a protective screen enclosure, creating a serene swimming environment. Lush greenery surrounds the pool area, and a guesthouse is visible in the background, featuring a simple facade with a centrally located door.

Guesthouse in Homestead

4.97 out of 5 average rating, 174 reviews

Charming Private Pool house for two.

Charming private back pool house on a fenced property in a quiet neighborhood close to US 1, the Turnpike, the Keys, Nascar and the Homestead Speedway, and the Everglades. You are 15-20 minutes from the Speedway, 20 minutes from the Everglades, and 30 minutes from Key Largo. For guests wishing to stay a month or more, I would require you to provide a copy of your photo ID.

Guest favorite

An arched wooden gate displays the number '231' and opens to a stone pathway lined with palm trees. Lush greenery and a vibrant flowerpot add a welcoming touch, leading to a courtyard area in the distance.

Guesthouse in Fort Lauderdale

4.92 out of 5 average rating, 193 reviews

Villa with Heated Pool, Laundry, Ping Pong & More

Romantic, clean, private and quiet: perfect to relax after a day at the beach or work. Modern décor, high end appliances and furniture, 82inch Samsung smart TV with Bose soundbar, private gazebo with grill. Just 3 miles from the beach and 1 mile from main highway i95 and 1 mile from Wilton Manors. Walking distance to grocery stores, bars and restaurants.